156661-42-6Relevant articles and documents
Reactivity of Lysine Moieties toward γ-Hydroxy-α,β-unsaturated Epoxides: A Model Study on Protein-Lipid Oxidation Product Interaction
Lederer, Markus O.
, p. 2531 - 2537 (1996)
Epoxyols are generally accepted as crucial intermediates in lipid oxidation. The reactivity of γ-hydroxy-α,β-unsaturated epoxides toward lysine moieties is investigated, employing trans-4,5-epoxytrans-2-hexen-1-ol (EH) as a model substrate and propylamine or N2-acetyl-L-lysine 4-methylcoumar-7-ylamide (AcLys-MCA) as model reagents for protein-bound lysine. Independent syntheses are reported for EH and AcLys-MCA. Reaction of the amine components with EH in THF yields 4-(propylamino)-trans-2-hexene-1,5-diol and N2-acetyl-N6-(1,5-dihydroxy-trans-2-hexen-4-yl)-L-lysine 4-methylcoumaryl-7-amide, respectively. Unequivocal structural characterization of the products prove the epoxy ring cleavage to proceed by a true SN2 mechanism. Incubation of EH with propylamine and AcLys-MCA in aqueous medium at 37 °C shows the turnover to decrease with lower pHs. From reaction of EH (100 mM) with AcLys-MCA (50 mM) under physiological conditions (pH 7.4), 3% of the lysine moieties can be identified in the form of N2-acetyl-N6-(1,5-dihydroxy-trans-2-hexen-4-yl)-L-lysine 4-methylcoumar-7-ylamide after 24 h.
Novel hydroxamates as therapeutic agents
-
Page/Page column 20, (2010/02/14)
The present invention is directed to certain hydroxamate derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes f
